How to get the most out of coaching in product

Lily Smith and Randy Silver turn the tables on each other in this deep-dive episode on coaching — what it actually is, how it differs from mentoring, and how both hosts have developed their practice over the years. From triad coaching programs at BBC Maestro to gestalt-based team coaching diplomas, they share hard-won lessons on holding space, the optimistic stance, and why the person being coached always has to do the work.

We discuss:

— Why Randy started coaching badly and by accident — and what he has learned since
—The difference between coaching and mentoring, and why most product people actually want both
— Lily's experience of being coached for the first time and realising she had to do all the work herself
— How to prepare for a coaching session and what to think about before you walk in
— The triad coaching model, liberating structures, and how to run peer coaching inside a business
— What gestalt-based coaching is and why the optimistic stance changes how you help people notice their own behaviour
— When to end a coaching relationship — and the value of ad hoc "unstuck" sessions
— Using AI and LLMs as a coaching substitute, and where human connection still has the edge
— Randy's AI chief of staff experiment — how a daily Slack prompt is making him less scattered
— The "coach bot" question: would you use a trained AI version of your coach?

Chapters
00:53 — Introduction: why coaching is back on the agenda
02:13 — How Randy started coaching (badly, and by accident)
03:06 — Coaching credentials, the ICF, and the mentor-coach hybrid
05:05 — Lily's 12-week coaching course and the triad program at BBC Maestro
06:22 — What it feels like to be coached for the first time
09:27 — When is the right time to get a coach?
10:46 — How to prepare for a coaching session
12:34 — Triad coaching, liberating structures, and Troika consulting
13:38 — What gestalt coaching is and how it works in groups
14:53 — The optimistic stance: why telling people they're wrong doesn't work
18:12 — When to end a coaching relationship
21:06 — Ad hoc "unstuck" sessions for leaders who can't admit they're stuck
23:28 — Using LLMs as a coaching tool: Lily's ChatGPT experiment
25:04 — Randy's AI chief of staff: Dex, RunOC, and a daily Slack check-in
26:44 — Can AI replace a human coach? Where the limits are right now
29:36 — How coaches are using AI tools to improve their practice
30:34 — Coach bots: training an AI on a coach's content and what could go wrong